Sydney Douglas was born a month before Brenda and spent the first four years of her life living in toddler bliss with her parents (her mother being Margaret's sister). Until one night, when her father caught a robber in the midst of robbing the house and subsequently got himself and Syd's mother killed. Being orphaned, Shy was given to Margaret and Bernard Chenowith. The Chenowiths adopted poor Syd and even gave her their last name. Syd and Brenda were four years old and Billy was just an infant, and their little family was complete. Syd's presence also fueled research and experimentation of the effects of death on a toddler's psyche. Where Brenda was Charlotte Light and Dark, Syd was Samantha Life and Death, the sequel written by the same Psychiatrist. Growing up in the same atmosphere as Brenda and Billy, Syd was also the product of two psychotherapists: overly analytical and overly skeptic of everything, as well as psychologically scared from everything. After unsuccessful run away attempts as a teenager, Syd left home for good when she was eighteen, but returned shortly after, after finding out about Billy's suicide attempt. Shortly after, he was diagnosed with Bipolar disorder, keeping her around for a while longer. She left for good November of 2000, when she walked out of the house at six am and never returned, keeping in contact with Brenda and Brenda only (for reasons we will discuss later). Three years prior, when Brenda left LA, she went to Syd, and together they turned their lives around. However, after Brenda left, Syd disappeared again, this time telling no one her whereabouts. Without contact with her siblings, Syd hit rock bottom. This brings us to the present, with Syd's sudden arrival at Brenda and Nate's wedding.